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> My claim was that sending electronic mail is a solved problem, because it is.

Agreed. I mean, I can _probably_ remember enough to be able to send mail using just telnet without even needing to look anything up. (And that mail, without any mime parts or urls - it very very likely to not fall into any of the spam filtering on my inbound email accounts...)




In the modern era, lots of mailservers run software that looks for weirdnesses in incoming email. I don't know, but I'd suspect that the typing delays of using telnet to send mail are likely to trigger their defenses.


SO I just tested. After working out that on macOS I now need to use nc -c instead of telnet... I _can_ send mail manually, but it _does_ end up in gmails's spam folder saying "Why is this message in spam? It is similar to messages that were identified as spam in the past."

  Iain-2:~ iain$ nc -c gmail-smtp-in.l.google.com 25
  220 mx.google.com ESMTP k5si5682618pls.209 - gsmtp
  EHLO elided.org
  250-mx.google.com at your service, [202.171.181.100]
  250-SIZE 157286400
  250-8BITMIME
  250-STARTTLS
  250-ENHANCEDSTATUSCODES
  250-PIPELINING
  250-CHUNKING
  250 SMTPUTF8
  MAIL FROM: <bigiain@elided.org>
  250 2.1.0 OK k5si5682618pls.209 - gsmtp
  RCPT TO: <bigiain@gmail.com>
  250 2.1.5 OK k5si5682618pls.209 - gsmtp
  DATA
  354  Go ahead k5si5682618pls.209 - gsmtp
  Subject: Test
  From: bigiain@elided.org
  To: bigiain@gmail.com
  Date: Fri, 31 Jan 2020 13:07:00 +1100
  
  Foo baz nah
  
  .
  
  250 2.0.0 OK  1580436443 k5si5682618pls.209 - gsmtp
  QUIT
  221 2.0.0 closing connection k5si5682618pls.209 - gsmtp
  Iain-2:~ iain$


I wonder why google treats this simple email as spam. It contains nothing that should trigger the spam filter aside from where it came from.


Most mailservers don't send emails one character at a time. You appear to have a mental model of how a spam filter works that doesn't include fingerprinting the behavior of the sending server? Even open source mail servers do that, for example postscreen is a part of postfix.


I wonder if it'd fare better if I scripted nc with expect?

(Not sure I care enough to try...)


Where it came from is one of the most important details!

Is this mail relay actually elided.org or is it impersonating elided.org?

There does not appear to be an SPF record for that domain so Gmail cannot determine if this is a fraudulent message, especially if the machine this request came from does not match the IP of the A record for that domain.


Some of the things it doesn't contain, though -- like Message-ID and Content-Type headers -- are likely to contribute to its spam score.

If your domain has SPF headers which don't permit mail from the (residential?) IP you're connecting from, that'll be a major factor as well.


Some years ago I wrote my email in a forum, available to crawlers. I’ve been getting spam ever since.




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